US5474872A - Polyvinyl alcohol-based photoresist - Google Patents

Polyvinyl alcohol-based photoresist Download PDF

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Publication number
US5474872A
US5474872A US08/250,530 US25053094A US5474872A US 5474872 A US5474872 A US 5474872A US 25053094 A US25053094 A US 25053094A US 5474872 A US5474872 A US 5474872A
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skeleton
group
composition
groups
development
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US08/250,530
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Yoichi Tomo
Masao Saito
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Sony Corp
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Sony Corp
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Assigned to SONY CORPORATION reassignment SONY CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SAITO, MASAO, TOMO, YOICHI
Priority to US08/438,832 priority Critical patent/US5550008A/en
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/106—Binder containing
    • Y10S430/11—Vinyl alcohol polymer or derivative

Definitions

  • This invention relates to a photoresistive composition and also to a method of forming a pattern using such a composition. More particularly, the invent ion provides a new photosensitive composition and also a method of forming a pattern using such a photoresistive composition.
  • the photoresistive composition and the pattern formation method according to the invention can be utilized for forming various patterns in the field of fabrication of electronic materials (such as semiconductor devices ).
  • a typical chemical amplification photoresist for instance of positive type, comprises a resin, a dissolution inhibition material and a photo acid generator (i.e., a photo-sensor).
  • a photo acid generator i.e., a photo-sensor
  • the dissolution inhibition material is not dissolved in aqueous alkaline solution (i.e., developer) for protecting the resin.
  • acid is generated from the photo acid generator, and the dissolution inhibition material is released by this acid to become soluble in the aqueous alkaline solution.
  • the acid acts as a catalyst and hence is not substantially consumed while progressively releasing the dissolution inhibition material.
  • the photoresist is called chemical amplification type.
  • a first object of the invention is to provide a new photoresist composition, which is suited for fine processes and can be actually utilized for various dry etching processes.
  • a second object of the invention is to provide an advantageous pattern formation method using such a photoresist composition.
  • a photoresist composition which comprises a substance containing a skeleton as at least a part of a main chain, the skeleton being obtained through polymerization of a vinyl alcohol type compound, at least some hydroxyl groups in the skeleton being protected by acid-releasing protective group, and a photo acid generator.
  • vinyl alcohol type compound is meant a compound which gives a polyvinyl alcohol chain (with or without a substitute group).
  • a photoresist composition as noted above, in which the substance containing a skeleton as at least a part of a main chain, the skeleton being obtained through polymerization of a vinyl alcohol type compound, at least some hydroxyl groups in the skeleton being protected by acid-releasing protective group, is represented by the following Formula (1) ##STR1## where R is a substitute group, at least some of the substitute groups R being protective groups R 0 capable of being released by acid.
  • a photoresist composition as noted above, in which the substance containing a skeleton as at least a part of a main chain, the skeleton being obtained through polymerization Of a vinyl alcohol type compound, at least some hydroxyl groups in the skeleton being protected by acid-releasing protective groups, is represented by the following Formula (2).
  • R 0 is a protective group capable of being released with acid
  • R 1 to R 4 are substitute groups, m:n being 1:9 to 7:3.
  • a photosensitive composition as noted above, in which the substance containing a skeleton as at least a part of a main chain, the skeleton being obtained through polymerization of a vinyl alcohol type compound, at least some hydroxyl groups in the skeleton being protected by acid-releasing protective groups, is represented by the following Formula (3).
  • R 0 is a protective group capable of being released by acid
  • R 1 to R 4 and R 1' to R 4' are substitute groups
  • m:(n+1) being 1:9 to 7:3.
  • a method of forming a pattern on an exposure material by using either of the above photosensitive composition development being done with a high polarity solution.
  • a high polarity solution water or aqueous solution mainly composed of water may be used when obtaining a positive pattern, and various alcohols, typically ethanol, may be used to obtain a negative pattern. It is further possible to obtain a negative pattern with ketones (e.g., acetone). While water or like aqueous solution is used to obtain a positive pattern, it is desirable to make development with hot water at 50° C. or above for realizing satisfactory development.
  • a method of forming a pattern as noted above in which rinsing is done with a low polarity solvent.
  • a low polarity solvent may be used various organic solvents which do not dissolve the pattern.
  • Examples of the protective group R 0 capable of being released by acid as noted above are class 2nd and 3rd alcohol carboxylate represented as ##STR4## substitute groups containing ether bond, such as ethylvinyl ether represented as ##STR5## and tetrahydropyranyl ether represented as ##STR6## and Ac acetate.
  • the substitute groups R other than R 0 are suitably those which can enhance the etching resistance.
  • Examples of such group are the adamantyl group represented as ##STR7## norbonyl group as ##STR8## cyclohexyl group as ##STR9## t-butyl group as ##STR10## and cyclopentyl group as ##STR11##
  • OH (hydroxyl group) and Ac (acetate group) may be present as residue.
  • R 0 and other group R may be made integral to provide the following partial acetonide structure. ##STR12##
  • the skeleton Of the composition may be made more chain-like and less subject to main chain breakage to increase the dry etching resistance. It is thus possible to obtain a photoresist composition, which can find suitable applications as resist materials exclusively used for ArF laser radiation or EB and X-rays.
  • the main skeleton of the composition according to the invention is obtained through polymerization of a vinyl alcohol type compound such as polyvinyl alcohol and those which are partially esterified (e.g., vinyl acetate).
  • a vinyl alcohol type compound such as polyvinyl alcohol and those which are partially esterified (e.g., vinyl acetate).
  • Protective groups for release protection with acid are introduced into a portion of the hydroxyl groups. Further, into a portion of the hydroxyl groups may suitably be introduced adamantyl or like substitute groups which impart with the dry etching resistance as noted above.
  • the groups that are to be substituted for are as exemplified above.
  • the group to be substituted is an ether type protective group
  • the hydroxyl group is protected by using paratoluene sulfonic acid or like acid catalyst with methylene chloride as the solvent.
  • the protective group is a carbonate
  • the corresponding chloride carbonate is reacted in ether or like solvent by using such basic catalyst as triethylamine, pyridine, etc.
  • R 0 and other R are integral and thus providing a partial acetal structure (such as acetonide)
  • reaction with the corresponding acetone and cyclohexane is brought about while azeotropically removing water with benzene or the like by using a Deanstalk type azeotropic apparatus.
  • this type of resin is commercially available as polybutyral resin.
  • Suitable examples of the protective group R 0 to be released with acid according to the invention are THP (tetrahydropyranile group), EE (ethylvinyl ether), t-BOC (t-butyl carbonate), etc.
  • R 1 to R 4 and R 1' to R 4' are hydrogen, halogen atoms (e.g., Cl), alkyl groups (including substituted alkyl groups, e.g., methyl group, ethyl group, --CH 2 Cl, etc.), allyl group (e.g., phenyl group), --CO.OQ (Q representing methyl group, ethyl group, isopropyl group, butyl group, t-butyl group, cyclohexane group, etc.), --COQ, --OAc, --CN, etc.
  • halogen atoms e.g., Cl
  • alkyl groups including substituted alkyl groups, e.g., methyl group, ethyl group, --CH 2 Cl, etc.
  • allyl group e.g., phenyl group
  • --CO.OQ Q representing methyl group, ethyl group, isopropyl group, butyl group, t-but
  • the following table shows examples of the combination of R 1 to R 4 to obtain photoresist compositions.
  • R 1' to R 4' can be provided by the above combinations.
  • photoresistive compositions which are excellently transparent and suitable as resist materials for KrF or ArF eximer laser. These compositions have high dry etching resistance 3compared to the PMMA type resists.
  • these photoresist compositions are copolymers and are thus very highly heat-resistant, and thus they have high dry etching resistance.
  • the weight ratio of the composition can be adjusted by the incorporation ratio or the like. If m is too small, it is undesired because dissolution in water can no longer be obtained.
  • Copolymerization of the vinyl alcohol units with comonomer mainly permits increase of Tg (glass transition point (softening temperature)) over pure polyvinyl alcohol.
  • Tg glass transition point (softening temperature)
  • Tg can be increased by increasing the molecular weight. With a positive type material, however, it is unsuitable to increase the molecular weight too much.
  • These materials can be synthesized by introducing protective group through ester exchanges of a vinyl alcohol type compound as the starting material of vinyl alcohol, such as vinyl acetate, and an acetate body, for instance, obtainable through emulsifying copolymerization of the corresponding vinyl compound, with a compound containing corresponding protective group for the portion of hydroxyl group only.
  • a vinyl alcohol type compound as the starting material of vinyl alcohol, such as vinyl acetate, and an acetate body, for instance, obtainable through emulsifying copolymerization of the corresponding vinyl compound, with a compound containing corresponding protective group for the portion of hydroxyl group only.
  • the ester exchange may be made with ##STR17## if the protective group to be introduced is ##STR18##
  • the corresponding acetate body of the material is obtainable by the following method.
  • Vinyl acetate and a vinyl compound are mixed using such an emulsifier as "Noigen YX-500", “Emal-O”, etc.
  • the mixture is then polymerized using an aqueous solvent and adding potassium persulfate, ammonium persulfate, etc. and acidic sodium sulfite, sodium sulfonate, sodium phosphate, etc.
  • the polymer is then salted out and then water washed to obtain the acetate body.
  • Such acetate bodies contains alkali metals, and therefore it is preferred to use ammonium bodies.
  • photoacid generator may be used those in Formulas 1 to 13 below. ##STR21##
  • FIG. 1 is a graph showing the relation between normalized thickness and exposure in Embodiment 4 of the invention.
  • Protective groups R 0 and substitute groups R 10 other than the protective groups as shown in Table 2 below were added in amounts as shown in Table 2 to polyvinyl alcohol resin, and optical acid generators as shown in Table 2 were added in amounts as shown in Table 2. Photoresist compositions were thus obtained, which were photoresist materials capable of development with water.
  • an ArF eximer laser contraction projection exposure apparatus with a contraction factor of 10:1 manufactured by Raser Ramder Figic
  • a 5-inch silicon wafer was used as the pattern formation material.
  • Each of the resins A to F noted above was dissolved in ethyl cellosolve acetate to produce a coating solution, which was then spin coated on a silicon wafer surface treated with HMDS, followed by baking at 90° C. for 90 seconds to obtain a film with a thickness of 0.7 ⁇ m.
  • the film was then exposed using a stepper and by varying the exposure amount and focus using masks with patterns of 0.1 to 0.4 ⁇ m line-and-space (with a pitch of 0.02).
  • post exposure baking PEB was performed at 110° C. for 90 seconds, then paddle development was done with water: for 60 seconds, and then rinsing was done with xylene.
  • Etching was done with an Electrochemical reaction (ECR) etcher by using blend gas of Cl 2 and CCl 4 .
  • ECR Electrochemical reaction
  • Table 3 shows the threshold resolution and the etching speed.
  • the etching speed is shown in terms of the speed ratio with the etching speed of m-p cresol novolak with a molecular weight of 5,000 as unity speed.
  • compositions No. 1 to No. 11 shown in Table 1 noted above were used.
  • the polymerization of the copolymer was set to 1:1.
  • the same exposure material as in Embodiment 1 was used.
  • As the development paddle development was done with water for 60 seconds.
  • As the baking conditions pre-baking was done at 100° C. for 100 seconds, PEB was done at 110° C. for 90 seconds, and after-baking was done at 150° C. for 120 seconds.
  • ECA ethyl cellosolve acetate
  • the exposure was done in two ways, when using KrF eximer stepper and when using ArF eximer stepper.
  • this embodiment it is possible to provide a photoresist capable of development with water, kind to environment, and having excellent dry etching resistance, high Tg, and high permeability to the Ar eximer laser beam (193 nm) and KrF eximer laser beam (248 nm).
  • butyral resin (1) shown below was used as the substance containing a skeleton as at least a part of a main chain, the skeleton being obtained through polymerization of a vinyl alcohol type compound, at least some hydroxyl groups in the skeleton being protected by acid-releasing protective group.
  • the butyral resin used had an acetylation factor of 70 mol % or above.
  • the optical acid generator was used the exemplified compound 7 noted above (i.e., triphenylsulfonium triflate).
  • the film thus obtained was pre-heated at 90° C. for 90 seconds. Then, it was exposed to KrF eximer laser beam (or ArF eximer laser beam), and then PEB (post-exposure baking) was done at 80° C. for 90 seconds, followed by development with hot water at 80° C. for several minutes, thus obtaining a satisfactory positive pattern.
  • KrF eximer laser beam or ArF eximer laser beam
  • PEB post-exposure baking
  • the butyral resin (2) used in Embodiment 3 permits a negative pattern to be obtained by development with alcohol.
  • the same exemplified compound (triphenylsulfonium triflate) as in Embodiment 3 was used as the optical acid generator. 0.18 g of this optical acid generator was dissolved in ECA (ethyl cellosolve acetate) to obtain 13.08 g of solution. 1.07 g of butyral resin (1) noted above was then dissolved in 1.07 g of the solution, and the resultant solution was passed through a 0.2 ⁇ m membrane filter and then spin coated on a Si wafer.
  • FIG. 1 shows the characteristic (i.e., relation between normalized thickness and exposure).
  • the photoresist composition used in Embodiments 3 and 4 can be said to be suitable for fine processes with KrF or ArF eximer laser beam.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
US08/250,530 1993-05-31 1994-05-31 Polyvinyl alcohol-based photoresist Expired - Fee Related US5474872A (en)

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US08/438,832 US5550008A (en) 1993-05-31 1995-05-11 Method for making a dry etching resistant positive and negative photoresist

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JP5-153044 1993-05-31
JP15304493 1993-05-31
JP6-000971 1994-01-10
JP00097194A JP3339157B2 (ja) 1993-05-31 1994-01-10 感光性組成物及びパターン形成方法

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5626782A (en) * 1994-10-12 1997-05-06 Mitsubishi Denki Kabushiki Kaisha Postexposure baking apparatus for forming fine resist pattern
US5738975A (en) * 1993-12-28 1998-04-14 Nec Corporation Photosensitive resin and method for patterning by use of the same
EP0877294A1 (en) * 1996-01-26 1998-11-11 Nippon Zeon Co., Ltd. Resist composition
US5866304A (en) * 1993-12-28 1999-02-02 Nec Corporation Photosensitive resin and method for patterning by use of the same
EP0982628A2 (en) * 1998-08-26 2000-03-01 Sumitomo Chemical Company, Limited A chemical amplifying type positive resist composition
US6060212A (en) * 1998-06-11 2000-05-09 Clariant Finance (Bvi) Limited 193 nm positive-working photoresist composition
US6344304B1 (en) * 1993-12-28 2002-02-05 Fujitsu Limited Radiation sensitive material and method for forming pattern
DE10203839B4 (de) * 2002-01-31 2007-10-18 Infineon Technologies Ag Resist für die Fotolithografie mit reaktiven Gruppen für eine nachträgliche Modifikation der Resiststrukturen
US9291904B2 (en) 2006-12-25 2016-03-22 Fujifilm Corporation Pattern forming method, resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method

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US6057083A (en) 1997-11-04 2000-05-02 Shipley Company, L.L.C. Polymers and photoresist compositions
US7804115B2 (en) 1998-02-25 2010-09-28 Micron Technology, Inc. Semiconductor constructions having antireflective portions
US6274292B1 (en) * 1998-02-25 2001-08-14 Micron Technology, Inc. Semiconductor processing methods
JP3798552B2 (ja) * 1998-04-23 2006-07-19 東京応化工業株式会社 化学増幅型ホトレジスト
US6426175B2 (en) 1999-02-22 2002-07-30 International Business Machines Corporation Fabrication of a high density long channel DRAM gate with or without a grooved gate
US6319655B1 (en) * 1999-06-11 2001-11-20 Electron Vision Corporation Modification of 193 nm sensitive photoresist materials by electron beam exposure
JP5042520B2 (ja) * 2006-04-26 2012-10-03 株式会社クラレ ポリビニルアルコール系重合体およびその製造方法
JP5277203B2 (ja) * 2006-12-25 2013-08-28 富士フイルム株式会社 パターン形成方法、該パターン形成方法に用いられる多重現像用ポジ型レジスト組成物、該パターン形成方法に用いられるネガ現像用現像液及び該パターン形成方法に用いられるネガ現像用リンス液
JP4551970B2 (ja) 2007-06-12 2010-09-29 富士フイルム株式会社 ネガ型現像用レジスト組成物及びこれを用いたパターン形成方法
JP2012012618A (ja) * 2011-10-21 2012-01-19 Kuraray Co Ltd ポリビニルアルコール系重合体およびその製造方法

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US3498786A (en) * 1968-08-12 1970-03-03 Kalvar Corp Vesicular materials and methods of use
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US4895788A (en) * 1985-08-02 1990-01-23 Hoechst Celanese Corporation Water developable lithographic composition
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Cited By (20)

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US7465529B2 (en) 1993-12-28 2008-12-16 Fujitsu Limited Radiation sensitive material and method for forming pattern
US5738975A (en) * 1993-12-28 1998-04-14 Nec Corporation Photosensitive resin and method for patterning by use of the same
US5866304A (en) * 1993-12-28 1999-02-02 Nec Corporation Photosensitive resin and method for patterning by use of the same
US20040202961A1 (en) * 1993-12-28 2004-10-14 Fujitsu Limited Radiation sensitive material and method for forming pattern
US7179580B2 (en) 1993-12-28 2007-02-20 Fujitsu Limited Radiation sensitive material and method for forming pattern
US20070037090A1 (en) * 1993-12-28 2007-02-15 Fujitsu Limited Radiation sensitive material and method for forming pattern
US6344304B1 (en) * 1993-12-28 2002-02-05 Fujitsu Limited Radiation sensitive material and method for forming pattern
US6790589B2 (en) 1993-12-28 2004-09-14 Fujitsu Limited Radiation sensitive material and method for forming pattern
US5626782A (en) * 1994-10-12 1997-05-06 Mitsubishi Denki Kabushiki Kaisha Postexposure baking apparatus for forming fine resist pattern
EP0877294A1 (en) * 1996-01-26 1998-11-11 Nippon Zeon Co., Ltd. Resist composition
EP0877294A4 (en) * 1996-01-26 1999-09-29 Nippon Zeon Co COMPOSITION OF RESIST
US6309795B1 (en) 1996-01-26 2001-10-30 Nippon Zeon Co., Ltd. Resist composition
US6060212A (en) * 1998-06-11 2000-05-09 Clariant Finance (Bvi) Limited 193 nm positive-working photoresist composition
EP0982628A2 (en) * 1998-08-26 2000-03-01 Sumitomo Chemical Company, Limited A chemical amplifying type positive resist composition
SG85129A1 (en) * 1998-08-26 2001-12-19 Sumitomo Chemical Co A chemical amplifying type positive resist composition
US6239231B1 (en) 1998-08-26 2001-05-29 Sumitomo Chemical, Company Limited Chemical amplifying type positive resist composition
EP0982628A3 (en) * 1998-08-26 2000-05-03 Sumitomo Chemical Company, Limited A chemical amplifying type positive resist composition
DE10203839B4 (de) * 2002-01-31 2007-10-18 Infineon Technologies Ag Resist für die Fotolithografie mit reaktiven Gruppen für eine nachträgliche Modifikation der Resiststrukturen
US9291904B2 (en) 2006-12-25 2016-03-22 Fujifilm Corporation Pattern forming method, resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method
US9465298B2 (en) 2006-12-25 2016-10-11 Fujifilm Corporation Pattern forming method, resist composition for multiple development used in the pattern forming method, developer for negative development used in the pattern forming method, and rinsing solution for negative development used in the pattern forming method

Also Published As

Publication number Publication date
JPH0749568A (ja) 1995-02-21
KR100295541B1 (ko) 2001-09-17
US5550008A (en) 1996-08-27
JP3339157B2 (ja) 2002-10-28

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